Dimethylformamide → HCID 86705028、化合物

HRID 1518703ノート

反応式

HRID 1518703 の反応式
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19](O)=[O:20])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[CH:24][CH:23]=3)[CH:15]=2)=[CH:10][CH:9]=1.[CH3:32][N:33]([CH:35]=O)[CH3:34].C(N(CC)CC)C.Cl.[CH3:45][NH:46][O:47][CH3:48]>ClCCl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([C:19]([N:46]([O:47][CH3:48])[CH3:45])=[O:20])=[C:16]([C:22]3[CH:23]=[CH:24][C:25]([S:28](=[O:31])(=[O:30])[N:29]=[CH:35][N:33]([CH3:32])[CH3:34])=[CH:26][CH:27]=3)[CH:15]=2)=[CH:10][CH:9]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68285339HCID 68285339、化合物2 回

生成物 1

HCID 86705028HCID 86705028、化合物収率 65.69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Oxalyl chloride (0.70 g, 0.48 ml, 5.58 mmol) was added drop wise at 0° C. to a solution of 5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 33c, 1.10 g, 2.79 mmol) in a mixture of dichloromethane (30 ml) and DMF (0.40 g, 0.43 ml, 5.58 mmol). The mixture was then allowed to warm to room temperature and stirred for 1.5 hr under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was dissolved in dry dichloromethane (30 ml) and the mixture was then cooled to 0° C. To the cooled mixture was added triethylamine (1.69 g, 2.32 ml, 16.75 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.54 g, 5.58 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with DCM (25 ml) and washed with water (2×25 ml) and organic layer so obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by flash column chromatography using 0.8% methanol in DCM as an eluent to obtain the title compound (0.9 g, 65.69%).

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturethe mixture was then cooled to 0° C
  4. stirringunder stirring
  5. stirringThe reaction mixture was then stirred at room temperature for 2 hr
  6. washwashed with water (2×25 ml) and organic layer
  7. customso obtained
  8. dry with materialwas dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a crude product
  11. customThe crude product was then purified by flash column chromatography

出典と根拠

ORDレコード
ord-a083a12e44c94e3dbb0ec88218383b0a
出典データセット
uspto-grants-2015_07
特許番号
US09072731B2

反応ノート

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